Regio- and stereoselective 6-exo-trig radical cyclisations onto chiral perhydro-1,3-benzoxazines:: synthesis of enantiopure 3-alkylpiperidines

被引：26

作者：

Pedrosa, R ^{[1
]}

Andrés, C ^{[1
]}

Duque-Soladana, JP ^{[1
]}

Rosón, CD ^{[1
]}

机构：

[1] Univ Valladolid, Fac Ciencias, Dept Quim Organ, E-47011 Valladolid, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 13期

关键词：

D O I：

10.1016/S0957-4166(00)00230-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Enantiopure 3-alkyl substituted piperidines are prepared by diastereoselective 6-exo-trig cyclisation of perhydro-1,3-benzoxazines derived from (-)-(8)-amino menthol. The diastereoselective cyclisation is promoted by tributyltin hydride, and the competitive 1,5-hydrogen migration depends on the position of the acceptor double bond and the radical site. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：2809 / 2821

页数：13

共 9 条

[1] Regio- and stereoselective 5-exo radical cyclizations on a chiral perhydro-1,3-benzoxazine moiety.: An access to enantiopure 3-alkylpyrrolidines
Andrés, C
Duque-Soladana, JP
Pedrosa, R
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12): : 4273 - 4281
[2] Regio- and stereoselective methoxyselenenylation of chiral 2-vinyl perhydro-1,3-benzoxazines promoted by selenium-heteroatom nonbonded interactions
Pedrosa, R
Andrés, C
Arias, R
Mendiguchía, P
Nieto, J
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (06): : 2424 - 2428
[3] Regio- and diastereoselective tandem addition-carbocyclization promoted by sulfanyl radicals on chiral perhydro-1,3-benzoxazines
Pedrosa, R
Andrés, C
Duque-Soladana, JP
Maestro, A
Nieto, J
TETRAHEDRON-ASYMMETRY, 2003, 14 (19) : 2985 - 2990
[4] Total regio- and stereoselective synthesis of perhydropyrrolo[3,4-c]pyrazole derivatives by [3+2] intramolecular dipolar cycloaddition reaction on chiral perhydro-1,3-benzoxazines
Pedrosa, R
Andrés, C
Maestro, A
Nieto, J
SYNTHESIS-STUTTGART, 2003, (09): : 1457 - 1461
[5] Synthesis of enantiopure 3-azabicyclo[3.2.0]heptanes by diastereoselective intramolecular [2+2] photocycloaddition reactions on chiral perhydro-1,3-benzoxazines
Pedrosa, R
Andrés, C
Nieto, J
del Pozo, S
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (12): : 4923 - 4931
[6] A novel synthesis of enantiopure octahydropyrrolo[3,4-b]pyrroles by intramolecular [3+2] dipolar cycloaddition on chiral perhydro-1,3-benzoxazines
Pedrosa, R
Andrés, C
de las Heras, L
Nieto, J
ORGANIC LETTERS, 2002, 4 (15) : 2513 - 2516
[7] Tributyltin radical-induced addition-carbocyclization on chiral perhydro-1,3-benzoxazines:: a facile entry to enantiopure tin-containing auxiliaries
Andrés, C
Duque-Soladana, JP
Pedrosa, R
CHEMICAL COMMUNICATIONS, 1999, (01) : 31 - 32
[8] Lewis acid mediated diastereoselective keto-ene cyclization on chiral perhydro-1,3-benzoxazines: synthesis of enantiopure cis-3,4-disubstituted 3-hydroxypyrrolidines
Andres, Celia
Gonzalez, Israel
Nieto, Javier
Roson, Carlos D.
TETRAHEDRON, 2009, 65 (47) : 9728 - 9736
[9] Synthesis of Highly Enantioenriched 3,4-Dihydroquinolin-2-ones by 6-Exo-trig Radical Cyclizations of Axially Chiral α-Halo-ortho-alkenyl Anilides
Guthrie, David B.
Geib, Steven J.
Curran, Dennis P.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (42) : 15492 - 15500

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